


New York State of Mind

by Beckleybombshell



Category: Supernatural
Genre: Bartender Dean, Destiel - Freeform, Human Castiel, M/M, Megstiel - Freeform, New York City
Language: English
Status: In-Progress
Published: 2017-02-25
Updated: 2017-08-21
Packaged: 2018-09-20 09:54:23
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 12,965
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9485990
Author URL: https://archiveofourown.org/users/Beckleybombshell/pseuds/Beckleybombshell
Summary: Ah, New York City.Dean had been living in the city for the past seven years and absolutely considered himself a New Yorker. However, having spent the first sixteen years of his life in Lawrence, Kansas, he did have a southern drawl about him and was much more charming and kind then most other New Yorkers.Castiel really only enjoyed the company of his beautiful girlfriend, Meg Masters, and his older brother, Gabriel, outside of his quality time spent with Anna. He had met Meg during her first year at New York University and his first year as a TA.Everything is not what it seems. Life always had another magic trick up her sleeve. In a city of 8 million people will you every be able to truly find your soulmate?Only with a New York State of Mind.





	1. Dean Winchester

**Author's Note:**

> This is a work of fan fiction using characters from Supernatural, which is trademarked by Eric Kripke. All the characters are created and owned by Eric Kripke, and I do not claim any ownership over them. The story I tell here is my own invention, and it is not purported or believed to be part of Eric Kripke's story canon. This story is for entertainment only and is not part of the official story line. 
> 
> I am grateful to Mr. Kripke for his wonderful stories about Hogwarts, for without Supernatural, my story would not exist.

Ah, New York City. With a population of over 8 million people, this concrete jungle is world renowned, and goes by many names. The Big Apple, the City That Never Sleeps, the Melting Pot, just to name a few.

The ones who are tough enough to make it in the city refer to themselves as New Yorkers. They never take shit from anyone. This includes each other. New Yorkers are known to be among some of the rudest people in the country, though they don’t see it that way. They are simply too damn busy to give you the time of day.

In the Capital of the World what makes you think they would ever have time to deal with you?

However, there are pockets of people who do not fit the stereotype of a typical New Yorker. Among the raging oceans of endless people, these safe havens are like breaths of fresh air, and if you just so happen to haphazardly fall into one of these lifesaving pockets, you better hold on for dear life. Making sure you never let go for fear of drowning in the swarm of endless bodies.

The Village Underground was one of those places that felt like home away from home. Located in the basement of some apartments in Soho, it was a place you would walk right by without even noticing. Nearly invisible to those who didn’t know it was there. It was a nice escape from the hustle and bustle of day-to-day life in the big city.

The bar didn’t have a sign advertising it was a place of business. If patrons weren’t paying attention, they would fall down the flight of stairs it took to get to the basement where one was greeted by a red, wooden door. Upon entering, they found that it was no bigger than an average double wide house. It was a typical bar in the fact that it had low lighting, a black bar and a dartboard close at hand. The five bar stools frequently used by patrons matched the red entrance door.

Walking further towards the back was a stage for local musicians, poets, and stand-up comedians. The four round tables around it were coupled with a few chairs each. The bathrooms were to the left of the stage with the kitchen on the right. The Village Underground was a simple, homely, dive-bar that didn’t deserve a second glance.

Unless your name was Dean Winchester. This was where he could be found six days a week, behind the bar, slinging drinks.

Dean had been living in the city for seven years and absolutely considered himself a New Yorker. However, having spent the first sixteen years of his life in Lawrence, Kansas, he did have a southern drawl making him much more charming and kinder than most New Yorkers.

He left his hometown, not by choice, but rather by force. Right around the age when puberty rears its ugly head for teenagers, Dean started to realize that he was slightly different than his peers.

In the guy’s locker room after baseball practice, Dean started to catch himself staring, completely mesmerized, by the half naked boys walking around. It wasn’t as if it was new to him, being in the locker room getting changed, but it felt like he was seeing the male body for the first time. It made his lower stomach tingle in a way that he had never felt before.

Thankfully, no one ever caught him staring or they might have beat him worse than his dad did when he found out what Dean really was two years later.

“What do you mean you’re… _g_ _ay?_ ”

“Dad, it means I like guys. I’ve been this way for a while, and I wanted to tell you the truth. I don’t want to hide it any longer.”

John eyed him up and down, trying to make sense of what his eldest son had just told him. This kind of news travelled quickly through a small town. People were always quick to pass judgement on others. His calm, somewhat perplexed expression slowly morphed into a furious, bewildered look, his face grew more and more red by the second.

“NO!”

Dean didn’t know what to say. “No?”

“No. I didn’t raise a homo. You are not allowed to be… _gay_ , do you understand me?”

“Dad, it’s not like I chose to be like this. I was born—“

Dean didn’t have time to finish his sentence before John’s fist met the side of his face. Immediately knocking Dean to the ground, he realized he was in for it.

Twenty-four hours later, Dean was on a bus headed to New York City with only a few meager possessions. A bag of the basic necessities, clothes, his journal, and his late mother’s wedding ring which hung on a simple, silver chain around his neck. His mother, Mary, had passed when he was only four years old. Ever since the day he lost her , Dean had never taken it off. It was the only link he had to her.

Dean made sure to leave behind a note for his little brother, Sam, apologizing for leaving him alone with their father. He told Sam to always stay safe, keep his head down, and finish high school. That’s exactly what Sam did, and four years later he moved to the city to attend New York University. He had high hopes of pursuing his dream of one day being an activist lawyer for the LGBT community. Of course Sam was inspired by his brother and everything he went through to come out and be the person he always had been.

Dean’s first few years in the greatest city in the world were less than wonderful, to say the least. He had to learn how to fend for himself for the first time in his life. This meant that he spent those first years mostly living on the streets. Clean water and food were among the hardest necessities to find. If not for the trees and bridges in Central Park, shelter would have been difficult to find as well. The winters were the worst. The harsh unforgiving cold, wet weather made it almost impossible to stay warm and even more impossible to get a decent night’s rest.

One particular night, after what seemed like endless days of snow, Dean was huddled underneath his usual bridge, shivering, struggling to survive in the midst of the blizzard. He had been in the city for nearly two years and had yet to make any progress in his life. Now 18 years old, no one would hire him because he didn’t have a high school diploma or GED. If he was lucky enough to be considered for the job after learning he was living on the streets, no manager trusted him enough to give him the job.

Broken, cold, and alone Dean was ready to surrender to the below freezing temperatures. To just go towards the light at the end of the tunnel, certainly not a good thing to say the least. While slowly slipping into the afterlife, and unconscious Dean was picked up and carried away from the life-threatening elements by a total stranger who brought him into the safety of a one room studio. That studio belonged to a man by the name of Crowley.

A few years older than Dean, Crowley was 23 at the time he found Dean underneath the bridge hanging on for dear life that dreadful winter night. After nursing him back to health, giving him a roof over his head, and a job downstairs at the bar he worked at, Crowley became rather fond of Dean. Then again, when one really looked at Dean, who wouldn’t be found of him?

Dean was taller than the average guy, standing at about 6’1”, with short, spiky, sandy blonde hair, and green eyes that mimicked grass after a summer shower magnified the color. He had a slim, yet muscular build, and his legs bowed just slightly at the knee. But the part of him that sent both men and women over the edge was the painfully perfect shape of his lips.

They were plump, light pink, and somehow always had a shine to them even though he never used even the tiniest bit of chapstick. They were the kind of lips others could only dream about. Where one would wake up hot, sweaty, and a bit flustered in the downtown region, only to be disappointed that it was just a figment of the imagination.

As smitten as Crowley was for Dean, the feelings weren’t mutual. While Dean was insanely grateful and extremely indebted to Crowley for saving his life, the romantic feelings were never reciprocated. It had nothing to do with Crowley’s personality, he simply was not Dean’s type, physically. Standing almost half a head shorter than Dean, Crowley had the unfortunate bad luck of beginning to lose his hair in his early twenties while sporting a scruff of a beard year-round.

Although, he did have the most attractive accent due to having relocated from Scotland in his younger teenage years. He just wasn’t what Dean was looking for in a partner. Shame too, because they would’ve been cute together. But alas, a bromance was all that existed between the two men. They functioned well together not only when working behind the bar of the Village Underground, but as roommates in the studio apartment above the bar as well.

“Dean, fancy a fag and a chat?” handing Dean a cigarette before lighting his own.

It had been four years since that fateful day when Crowley had found Dean knocking on Death’s door. He had given Dean everything he needed to survive, a place to stay, a job to work at. He helped Dean get back on his feet after he had been tossed to the curb like a pile of trash by his unforgiving father.

Taking a drag and sliding it over an ashtray Dean breathed out a puff of smoke, “Yeah, what’s up?”

Crowley was sitting across that the bar, while Dean poured him a glass of Maker’s Mark whiskey. It was rather slow for a Sunday afternoon, besides the two of them, there was one other guy sitting at a table reading a script for a play. In New York City, that was a common sight. Thousands of struggling artists made their trek to the city every year in hopes of seeing their name up in lights, sadly though it rarely ever happened.

“We’ve been living together in that small ass flat for what, a few years now?” Crowley asked as he took a sip of his whiskey.

Dean nodded. “Four years.”

“Well, I think it’s time one of us moved out. It’s too bloody small for the both of us anymore. Whaddaya say?”

Just as Dean was about to protest, Crowley slid a single golden key across the bar.

“I already told the super you would be taking over the lease and told Bobby you’d cover all my shifts at the pub.”

Staring wide eyed at his best friend, Dean was at a complete loss for words. Crowley had been his lifeline for four years, and here he was up and moving without so much as a discussion about it.

“What the hell do you mean?” He asked flicking the ashes into the tray,” You’re moving out?”

Crowley laughed a bit and took another sip of his whiskey.

Burning like fire the whole way down, he coughed a bit and replied, “Yes, I’m moving out mate. I’ve been in America for too bloody long. My mum is back home and apparently, she’s gone completely mental. Claiming she’s a bloody witch running around town trying to hex people.”

Dean set his cigarette down in the ashtray, picked up the bottle of whiskey and a second glass and began to pour himself a drink. It wasn’t _necessarily_ against the rules to drink on the job, you just couldn’t lose control. And on a day like this, it wasn’t like he was going to need his full attention and focus for a basically empty bar.

Plus, he needed a stiff drink.

Taking it all in one swig, he slammed the glass down poured himself another and set the bottle on the bar, before finally looking at Crowley.

“And when were you planning to tell me this? I mean, what the fuck man. I live with you and you haven’t said a word about this until today. And now you’re just leaving? Just like that? Here’s the keys, see you later?”

Dean choked down the second glass of whiskey in a similar fashion as the first while Crowley did the same. He proceeded to pour them both another round as they each took a drag from their cigarettes before ashing them in the tray on the bar.

“Bloody hell Dean, it wasn’t like I got this news months ago, and stewed over it. My aunt called me this morning. It’s kind of urgent. They’re talking about locking Mum up in some institution.”

Dean looked down at his full glass, contemplating life without Crowley, his roommate, his co worker , his best friend. It seemed lonely, and cold, just like the night Crowley found Dean, curled up underneath that bridge. If Dean had been more of a softy, he would have let a few tears sneak past his eyelids, but years on the streets made him rough around the edges.

Dean let out a sigh he had been holding back before looking up to meet Crowley’s hazel eyes. “I don’t know what I am going to do without you.”

Crowley chuckled, “Where’s your Moose?”

Ah yes. Dean’s younger brother Sam whom Crowley had so affectionately named ‘Moose’ due to his gigantic stature. Sam had moved to New York a few months ago, at the beginning of August and currently resided in Brooklyn with a few of his college buddies. It’s not that Sam didn’t enjoy spending time with Dean, but it was that if he truly wanted to be a lawyer it meant having laser focus when it came to school. The few times he wasn’t nose deep in a textbook, or spending hours at the library, he did try to come see Dean. But those times were few and far between.

“You know Sam is busy with school.”

“I know, mate. I’m just pointing out the fact that you won’t be entirely alone like you think. Besides, with the flat all to yourself you can start bringing back all those boyfriends you’ve been hiding from me,” Crowley replied with a smirk, putting the last of his cigarette out.

Dean rolled his eyes and knocked back the whiskey in his glass. It was true, he had been out with a few guys in the past few years but he never brought them back to the apartment. Especially since it was a studio style, that would have been awkward to say the least.

“Look Dean, I know it’s a load of bollocks. But she’s my mum mate. I have to go back.”

“I know man. When do you leave?”

“My flight is in 3 hours.”

“WHAT THE FUCK CROWLEY! 3 HOURS?! THANKS FOR THE FUCKING NOTICE YOU SONOVABITCH!” Dean screamed so loudly that the poor lonely soul at the table jumped, startled with fright, looked up from his papers, promptly paid and got the hell out of the bar. Dean was terrifying when he was angry.

“You know I don’t do goodbyes, mate. I’m sorry I’m leaving right before the holidays, but I promise I’m going to plan a trip back across the pond for your birthday in January.”

Crowley casually picked up his glass of whiskey, swallowed it, set the glass on the counter and stood up. “Look mate, I’ll be back before you know it.”

Dean knew that this was the end of the conversation, so he walked around the bar, sulking the whole way, until he was standing in front of his best friend. He looked at him with a face full of resentment, fear, and anxiety. This was it. He was about to say goodbye to his one true best friend. The one who saved him from damnation. The one who took him in and cared for him when he was at his lowest. This was it. This was goodbye.

“Quit looking at me like I killed your bloody dog, Dean. This isn’t goodbye. It’s just until my bat shit crazy mother gets better, alright.”

“Yeah alright,” he said with more emotion than he wanted to. Maybe three whiskey shots in less than thirty minutes wasn’t his brightest idea.

 _No fucking chick flick moments_ , he thought to himself. _Get it together Dean._

The pair hugged goodbye and Dean walked him up the stairs to wait with Crowley until his shuttle for the airport arrived. Dean pulled a pack of cigarettes out of his jacket pocket and lit one before offering any to Crowley. He took a slow drag.

“These things will kill you, yaknow,” remarked Crowley as he too was taking a drag out of the white cylindrical cancer stick.

Dean shot him a sideways glance before exhaling right into his face.

“Shut the fuck up Crowley. You truly are the King of Hell, yaknow.”

Crowley let out a bellowing laugh before dropping his cigarette on the ground. Snuffing it out just as his shuttle pulled up to the curb. He turned to Dean and gave him one last hug before putting his lone suitcase in the back of the van.

“See you soon, Squirrel,” said Crowley just as he was climbing in and shutting the door of the van.

Dean stood there waving at him as he watched the shuttle drive to the end of the block and turn out of sight, heading for LaGuardia Airport. He took a few more drags of his cigarette before snuffing it out just as Crowley had done.

The chilling October air felt even more sinister with the knowledge that at the end of his shift tonight, he would be going home to an empty apartment. It’s not that Dean couldn’t handle being alone, it was the mere fact that he had gotten comfortable with the idea that someone was always there with him.

Crowley and he had shared basically one life for four years, and now that he was gone, who was going to be his guardian angel?

Dean shivered and put his cupped hands up to his mouth blowing on them for warmth, as he descended back down the stairs to his now empty bar. Opening the red, wooden door, he was greeted with the faint scent of stale beer, cigarettes and the ghost of his best friend. He walked up to one of the stools and sat down. He still had hours before the bar was due to close, but he had a faint feeling he wasn’t going to have any customers for the rest of the evening.

The owner, Bobby Singer, always let the boys close shop early on Sundays if they hadn’t made any money for a few hours. This seemed like the perfect time to do so. Not wanting to go back to an empty apartment, however, kept Dean from doing just that. It left him pondering what had just happened. His whole life had done a 180 and was now completely different then when he woke up this morning.

Still feeling the whiskey buzz from earlier, Dean decided to keep it going because, well, why the hell not. He poured himself another glass and pulled out his cell phone dialing the first number on speed dial.

_“Dean?”_

“Hey Sam. How’s the studying going?”

_“Good, I think I’m all caught up for next week. What’s going on?”_

“How soon can you get from Brooklyn to the bar?”

_“I’m actually at the library. Why? What’s up?”_

“Come drink with me.”

_“Uh, alright Dean. I’ll be there in 10.”_

Thankfully, Sam’s school library was closer to Soho then Brooklyn so it wouldn’t take much time at all for Sam to get to the bar. Bobby didn’t mind when Sam came and drank at the bar with Dean. Sam was only 18, but it was one of those, don’t ask, don’t tell situations. If Bobby never knew that Sam was drinking illegally, it didn’t really matter.

Which was lucky for Dean, because he needed his brother now more than ever. Even if his best friend in the world had just up and left him suddenly, without warning, at least he still had Sam. Without Sam, Dean would be hopelessly lost.

He took another shot of whiskey before walking towards the door and flipping the “Open” sign to “Closed”. He lingered at the window, staring blankly at the brick wall and stairs that were outside. He couldn’t see the street above him but he could hear it. All the sounds of the cars and people running from place to place in this enormous city.

 _I hope he brings me some fucking pie,_ thought Dean as he walked back to his bar stool pouring himself another whiskey.


	2. Castiel Novak

**Notes for the Chapter:**

> Slowly but surely, my beta and I are cranking this book out! We both have busy lives to tend to so updates I'm sure will be few and far between. Plus, I usually can only write when the inspiration strikes! 
> 
> This being my first fic though, I'm extremely honored to already have a few bookmark and a couple dozens views. It gives me goose bumps!
> 
> As always, read and review!
> 
> Enjoy!

Chapter 2

The smell of burnt coffee lingered throughout the third floor of the brownstone apartment, the source, a used and abused coffee maker with half a pot left in it. It was a cold, Saturday morning in mid-October. While most people took the opportunity to sleep in and recover from a grueling work week, this concept was lost on those who did not have the luxury of taking a day to rest. Namely, university students who wanted desperately to maintain a decent GPA. The ones who had dreams of someday nabbing that interview, or internship they had worked tireless hours for.

Higher education was considered non-optional if a student wanted to make something of themself. Back in the day, people could survive with hard work and determination, but in the 21 st century, this wasn’t the case. If you wanted to amount to anything, you went to college. With that came unimaginable amounts of pressure to succeed with not only good grades and a useable degree but also accomplish it in four years. Which, to be quite frank, was almost impossible unless you had unbelievable self-discipline or the brains of a Mensa member. However, some had managed to make it regardless of the unrealistic times table, and then thrusted themselves into grad school without so much as a cooling off period.

Castiel Novak had done exactly that. He slightly regretted it as he sat at the kitchen table in his two-bedroom Brooklyn apartment he shared with best friend, Anna. He casually looked up from the stacks of paper surrounding him on all sides, his task for the rest of the weekend. He had to get all these papers graded before Monday, and Anna was not helping him concentrate at all.

“Cas, what the hell are you doing?!”

She was running through the apartment like a red-headed tornado grabbing signs and fliers all while trying to put on her shoes. If it wasn’t for the fact that he had been so rudely interrupted, he would have found it quite amusing. Anna always had a way about her that made her seem almost whimsical in the way she went about conducting herself, even if it appeared chaotic. Standing at five foot and a half, with light eyes and hair like fire, she was quite a force to be reckoned with.

“You know I have work to do, Anna. Professor Mills isn’t going to be thrilled if I don’t get through all these papers this weekend.”

Castiel sighed as he thought about what really would happen if he didn’t get all these papers graded. He could lose his full ride scholarship to one of the best colleges in the country. Okay, that might be a bit over dramatic, but still meant running a risk he wasn’t willing to gamble.

New York University had become one of the largest private universities in the country and had branches across the globe. With an acceptance rate of 30% it was a rather prestigious school to be accepted to whether for an undergrad or graduate program. With that came many opportunities one otherwise wouldn’t have access to.  

Castiel was in his second year of grad school, it was proving to be much more challenging than his undergrad. Alright, maybe getting a bachelor’s degree in Philosophy wasn’t exactly amazingly academic. But a  _ Masters _ in Religious Philosophy would be at  _ least  _ impressive, if not uncomfortably intellectual. Castiel still had three years until graduating and he’d be damned it was going to all come crumbling down now.

“I know you worker bee,” Anna teased, as she was lacing up one of her boots. “But you  _ promised  _ me you would come to the Meat is Murder March with me this weekend.”

Had he promised that? Shit. He did.

But there was  **no way** he could sacrifice that kind of time this Saturday to help her with one of her hopeless political causes. Even if it was to save all those poor animals, marching about, yelling at people who eat meat wasn’t exactly how you went about changing someone’s mind on the subject. Especially in New York City. However, Anna seemed called into action every time she felt there was an injustice in the world, no matter how small.

“I thought Meg was going to accompany you?”

“Well, she is. But—“

“Anna, I have to get this done. I’m sorry. Next time okay? I promise.”

Great, did he just promise he’d go to the next one? He really needed to stop getting her hopes up that he actually cared about all these silly little causes she had. While he admired her tenacity, Castiel did find it rather irritating from time to time.

“You always say that and you never come! I swear, I don’t know what Meg sees in you,” she said as she completed lacing up her other boot. She hastily finished gathering her things and was running out the door before Castiel had the chance to reply.

He knew that he had blown Anna off, when he had promised so many times that it was now terribly embarrassing. His fierce and fiery red-headed roommate was the type of person whose heart was three times its normal size. Sometimes, he could swear she was somewhat angelic when it came to caring about others, not to mention she was always forgiving him for bailing.

_ Finally,  _ thought Castiel as he ran thin fingers through his tousled midnight black hair, before bringing both hands to either side of his face to massage his temples. He might actually be able to get some work done in his own apartment for a change without having to escape to the library. Which took twenty minute by train to get to the college, or if it was open Castiel would go to the local coffee shop two blocks away.

Being a TA had its advantages, and boy did it look good on a resume, but it was a rather tedious job. Most weekends, Castiel was tied down grading exams for his boss, Professor Mills. She was the head of the philosophy department at New York University, and his favorite professor during his undergrad. It was an honor to be studying his craft under her.

While Castiel did enjoy the sociable company of his lovely roommate Anna, it seemed that on the weekends, this rather small apartment of theirs was transformed into the gathering place for any and all social events of the weekend. It was as if they had a revolving front door which had people of all kinds coming in and out. Mostly people from Anna’s many groups and organizations she was involved with on campus.

So frankly, he was quite relieved she had a demonstration to attend today or the place would have been filled with a bunch of self-righteous hippies. Nice people, they just always tended to smell like cedarwood and the faint remains of marijuana smoke. While usually dressed in tie dye and sporting leather sandals.

He had known Anna for years before they decided to move in together. Even though they had gone to the same high school growing up, they ran in different social circles that never crossed paths. It wasn’t until the pair had bumped into each other during their first semester at college standing in line at a cafeteria that they started to spend time together. After completing their first year of college, they decided to become roommates since they spent all their time together anyway, it made logical sense.

They had been living together for five years in the apartment in Brooklyn and had many amazing memories of the place. Of course, the rumors had spread through their circle of friends that the two were dating, however, this was simply not the case. If one didn’t know any better, they would probably mistake them for being brother and sister. Lord knows they bickered like siblings, and honestly, Castiel considered her family. Which was saying something since he wasn’t exactly the social butterfly type.

Castiel really only enjoyed the company of his beautiful girlfriend of two years, Meg Masters, and his older brother, Gabriel, outside of his quality time spent with Anna. He had met Meg during her first year at the University and his first year as a TA in an Intro to Philosophy class.

Only having just graduated from his understudies program, he had not been particularly searching for, or even possessed the desire for a relationship beyond the few, short and sweet one-night encounters, but Meg had been extremely persistent.

She would show up to class dressed to the nines, complete with her dark brown waves done up just so, that when she walked they gave the appearance that she bounced with them. After a few weeks of painfully trying to attract his attention, Castiel had finally caved and asked her out. They had been together ever since.

To be quite honest, he wasn’t entirely certain as to how he suddenly found himself in a relationship with her. While it was obvious that Meg was attractive, she had “curves in all the right places”, as they say, Castiel just never really found her  _ that  _ physically magnetizing. However, he did enjoy the way her mind ticked away and how big of a caring heart she had, even though she tried to hide it. To him, that was enough of an attraction to keep him around. The sex was satisfying and enjoyable, so he saw no reason to not be with her. She respected his privacy and space, which he was grateful for being mostly an introvert, that was exactly what he needed.

Besides, Anna was her best friend, and with her being so fiery, Meg was never left without a partner in crime. When Castiel introduced them, the pair instantly clicked and started spending a lot of time together. Having been best friends for a few years now, they were almost inseparable. So, when Castiel needed his down time, Anna was more than willing to whisk Meg away to one of her marches, or causes at any given point.

Gabriel, however, was an entirely different story. A few years older than Castiel, he should have been the taller of the two but instead stood two inches in the shadow of his younger brother. That however did not slow him down one bit. He made up for it in pure sarcasm, which fueled the fire when it came to his standup comedy routine. Having graduated high school with absolutely zero aspirations of going to college, or receiving any form of higher education, Gabriel set forth to become the next Louis CK and took to the streets of New York City to follow his dreams.

The Novak brothers grew up three hours north of the city by train in a town called Poughkeepsie. Now, to some that may seem like worlds away, but these two spent many weekends catching the train out to the city just to run through the endless twists and turns of the concrete jungle. Of course, no parent in their right mind would let a couple of teenagers go off on their own to do this, so naturally they always told their parents they were at bible study like good boys. Please. They were teenagers.

Castiel had since grown out of that adolescent need to break and bend the rules and taken on a more respective and reserved tone which his parents were quite thankful for. The same could not be said for Gabriel, for he had spent the better part of a decade trying to “make it”. While simultaneously trying to save money with his starving artist status which caused him to be homeless most of his adult life. He had become quite skilled at the art of couch surfing and even retreated up north to his parents when he had worn out all his welcomes in the city.

Occasionally, he would come knocking on the apartment door of Anna and Castiel asking to bum around on their couch for a day or two but he understood how wound up that could make his brother so he never tried to push his luck. Even if Gabriel was kind of a low-life, he still possessed a sense of respect and self-preservation.

_ Ring – Ring. _

Castiel looked down at his phone to see who could possibly be interrupting his work when he had only just successfully gotten Anna out of the apartment. He nearly fell out of his chair when he realized four hours had passed since 10 this morning.

_ Ring – Ring. _

“Hello Gabriel,” Castiel sighed into the phone.

“ _ Hey, hey, hey, little brother! What’s shakin’ _ ?”

There was always a certain amount of playfulness in Gabriel’s voice that constantly made you question whether or not he was on drugs. He wasn’t of course, but Castiel always had that picture in his head.

“I’m working _. _ What do you want?”

“ _ It’s Saturday! Let’s hangout! I want to show you this really obscure bar I found in Soho and I was thinking— “ _

Castiel cut him off there. Gabriel  _ always  _ had found some new and ‘obscure’ place he wanted to do his comedy routine at and  _ always  _ insisted he check it out with him before performing so this wasn’t something exactly new or exciting.

“I can’t right now, Gabe. I have to finish this before Monday. Besides, it’s two o’clock in the afternoon. Who goes to a bar this early?”

Gabriel started to laugh on the other end of the line, “ _ Only the best and brightest stars, Cas! Only the best and brightest!” _

For someone who seriously needed to reconsider his career path in life, Castiel had to admire the man for withstanding all the negative blows and setbacks, he continued to be hopeful and optimistic about damn near everything in life. Something Castiel was rather jealous of.

“Next weekend, promise.”  _ Click.  _ Castiel did not give his brother a chance to reply. Yet another irritating yet admirable trait about Gabriel was his ability to talk.  _ A lot.  _ And frankly, Castiel lacked the patience to deal with the endless earfuls of this and that, what hobo had taken over which corner, and how many times this week he saw Elvis in Times Square. It was New York City, so it was a lot.

_ I seriously have to stop making all these promises,  _ Castiel thought as he pushed himself up from the table, causing the chair to slowly slide against the cool tile under him. He casually walked around the square table and turned the corner into the kitchen.

He went towards the coffee pot that had a glowing red light shining bright, indicating it was still on. He pressed the button to turn it off and promptly dumped the rest of the contents in the sink before replacing the pot back on the burner.

Castiel took another few steps to his right to open the fridge door. He stood in front of the ajar door for a solid 2 minutes before realizing his contacts were starting to dry out. Leaning his head down and bring up his left hand to his eye to rub, he thought about the grumbling noises that were reverberating out of his stomach reminding him that he had yet to eat that day.

After removing his hand and blinking several times, he searched the fridge looking for anything remotely edible. Scanning up and down the shelves, everything looked unappetizing and started to make him feel queasy. Although he couldn’t be sure if it was the food, or lack thereof, that was twisting his stomach up in knots or if it was all the coffee he had pounded down his throat for the past few hours.

_ Ring – Ring. _

Castiel looked up, right arm still on the edge of the refrigerator door. His eyes meeting a carton of half-drunk milk, realizing it had expired four days prior.

_ Ring – Ring. _

“What?” Castiel answered having not looked at the caller ID. The stress had finally begun to weigh down on his shoulders. He had two more months until Winter Break. Which might not have seemed like much to most people in their mid-twenties, but grad school had been particularly unforgiving to his sleep cycle and eating habits this semester.

“ _ I’m sorry. I did call Castiel my boyfriend _ ,  _ right?” _

Castiel sighed. He knew he loved Meg but god –

“Yes Meg,” Cas breathed, “I’m working. What do you need?”

_ “We told Anna we would come march with her. And since you aren’t here – “ _

He inhaled and held it in. He knew exactly what was coming. Every time, he fucking did this, every time he somehow got bogged down in work, it was always  _ his  _ fault for being a pushover .

“FINE. I’ll come to the after party. What time?”

_ “Eight. I’ll text you the rest of the details.” _

Castiel rubbed his eyes with his left forefinger and thumb. That gave him approximately five, no – four and half hours of pure concentration before he was going to be forcefully fed alcohol and social activity. Fabulous.

“Yeah, alright. Got it,” Castiel said quickly, avoiding any further argument.

_ “I love you.” Click. _

He shut the door of the fridge and walked out of the kitchen into the living room, winding his way between the couch and coffee table. Before coming to a stop at the window to peek out of the shades to the busy street below him. Castiel loved his life, he did, but he often thought there had to be more than this. There had to be something more than school, work, social events, obligations, responsibilities, all of it. He felt like his life lacked a sense of inspiration and adventure. He could recall a time when he first came to the Big Apple and felt like his life was full of magic and wonder, the whole world seemed big and bright and open, full of new discoveries. Now, years later, he just felt he was going through the motions of it all with no sense of real purpose.

Some would say this could easily be identified as depression, and to be frank, that’s exactly what was consuming Castiel. He could keep it together most days, but like all mental illnesses, some days were better than others and today was a particularly difficult day. He had felt this way for a few years now, but had always invented the best excuses for it. Too much sleep, not enough sleep, not enough sunlight, too much school work. He had become a master of avoidance, but the one person he could not avoid forever was himself.

Castiel couldn’t share this with any of this friends though, not even his brother or his girlfriend for that matter. He felt like this was a deep, dark secret that would be misunderstood if spoken out loud. This was a burden he chose to bear internally. Walking back towards the kitchen table to sit down and resume his work for the next few hours, he ran a hand lazily through his dark, disheveled hair as he pondered the weight of his dark inner voice.

**_There was more to life than this, wasn’t there?_ **


	3. Stranger in the Crosswalk

Though it had been two and a half weeks since Crowley had left the country, it felt more like a lifetime. Somehow Dean’s already small apartment managed to feel  _ even smaller _ since his best friend moved out. Sitting at the two-person kitchen table with a plate of scrambled eggs and slightly over cooked bacon, Dean stared down at his phone, taking a sip of orange juice.

He had been expecting a phone call this morning from Crowley but his phone had yet to ring once. Seeing as how they were now an ocean apart, competing time zones had made getting in touch a little tricky. It was around eleven in the morning which would put Crowley somewhere in the midafternoon given they had a five hour difference.

But nothing. No texts, no calls.

_ I got up early for this shit? _ Dean thought as he stood up, taking his half-eaten breakfast and glass to the kitchen sink. He turned on the facet, rinsing away what was left of his meal before pouring out the remainder of his glass. Setting them both in the sink, Dean turned around to lean against the counter. Crossing his arms he briefly stared off into space.

It wasn’t like Crowley to not keep his word. He was usually punctual and always honored his agreements, which sent a shiver of worry down Dean’s spine.

_ Where the hell is that asshole?  _ Dean thought as he pushed off the counter and began walking towards the bathroom. He contemplated what to do with his day now that he was already up and moving, it seemed like a waste to just head back to bed.

He hadn’t really done much since the sudden loss of his best friend except for working. He didn’t mind too terribly since now he was paying for the apartment on his own, he needed the extra income, working doubles at the bar was certainly in his favor. However, putting in roughly twelve hour shifts six days a week was taking its toll on him and Bobby had noticed.

He had given Dean the day off to “ _ Get some rest, ya idijt.”  _ But rest was the farthest thing from Dean’s mind.

He turned on the shower and stood in front of the mirror while the water started to heat up. Grabbing his toothbrush with his right hand, and toothpaste with his left, he promptly brushed his teeth, finishing just as the steam began to fog the mirror.

Shredding off his plain white t-shirt while kicking his dark grey boxers to the side, Dean stepped into the shower and pulled the curtain.

He let out a hissed scream, “Sonovabitch!”

The water had become scolding forcing Dean to quickly reach for the facet letting some cooler water balance out the intensity. He stood there with his head down, letting the water fall across his face, becoming lost in the heat that surrounded him and relaxed his muscles.

He thought about his mother. Dean was so young when she passed but he still had flashes of her locked away in his memory. He reached up to the chain that hung around his neck, wrapping his fingers around the silver ring that was suspended from it. This was the only thing he had left of his mom, Mary. Whenever he felt lost and alone he would hold onto it, and almost instantly would start to feel better, like she was watching over him from beyond.

Dropping the necklace back down to his chest, Dean shook his head in an attempt to physically wipe all the loneliness that was beginning to swallow him away. He turned around, allowing the water to roll over the muscles in his back and began his showering routine.

Dean stepped out of the shower into the steamy bathroom reaching for the fluffy red towel that dangled on its proper hook on the back of the bathroom door. First drying off to his face, then the rest of his body, Dean wrapped the towel around his waist and walked out of the bathroom.

He stopped abruptly at the kitchen table to pick up his phone.

One missed text message. It was from Crowley.

_ Hey mate, sorry I didn’t call. Had an emergency. Will try to call again soon. _

Dean sighed and set his phone back on the table. He knew that Crowley was dealing with a lot because of his sick mother but still it was painful to not have him by his side like he had been for the last few years. Dean tried not to let it get to him though because he knew Crowley wouldn’t have left him without a good reason.

He walked over to the closet in the corner of his open floor plan, pulled out a white V-neck and a faded pair of blue jeans, tossing both on the queen size bed behind him before moving to the dresser to the right. Opening the first drawer, Dean shuffled through the contents until he pulled out a pair of light grey wool socks, and black boxer briefs.

After getting dressed, Dean picked up his boots before walking backing to the kitchen table where he took a seat. As he began to put on his boots, his phone started to vibrate. He picked it up to read the screen. It was a text from Sammy.

_ Hey Jerk. I know you have today off. Get out of the house. Meet me at my apartment after class. _

It was Monday, that meant that Sam would be getting out of class roughly around 2pm. Dean looked at the clock in the kitchen, calculated he had roughly two hours until he needed to be on the train headed to Brooklyn, in order to meet his brother. He walked into the bathroom to check himself in the mirror one last time. It’s not like Dean ever had a day where he didn’t ooze attractive confidence, but today felt a little different. Today felt important.

Casually pushing those thoughts out of the forefront of his mind, Dean exited the bathroom, scooped up his cell and slide it in his back pocket. Grabbing his keys from the set of hooks to his right and grabbing the doorknob with his left  he paused to peak over his shoulder at his empty apartment.

_ I’ll never get used to this,  _ Dean thought as he slipped out into the hallway, locking the door behind him. Strolling towards the stairs passing his neighbors doors one by one, he fit his keys into the front pocket of his jeans and headed down to the first floor.

Walking out the main door of the building, Dean was greeted by a waft of cold, nearly freezing autumn air which alerted him that winter was just around the corner. He tugged at the collar of his jacket pulling it closer to his neck. The sounds of the street in front of him pierced his eardrums. The street was full of screeching car brakes, the occasional beeping of horns, and the rustle of people talking to each other, on their cellphones, or to themselves. He pulled his cigarettes out of his jacket breast pocket, picked a single white cylinder out of the bunch, before returning them to their home. Sparking up a match and inhaling deeply Dean almost missed the silence of his empty apartment upstairs.  _ Almost _ .

After standing in the same spot for a few minutes, smoking his cigarette and taking in his surroundings, Dean rounded the railing to the left and headed down the stairs to the bar, tossing the butt of the cigarette towards the street. Peaking in the window, the bar looked deserted, but for a Monday, mid-day, that was to be expected. He pushed through the front door and was greeted with the kindest welcome…

“What the hell are you doing here boy?”

Dean looked up and locked eyes with Bobby who was standing behind the counter, wiping a glass with a plain white towel.

“Calm down, old man. I’m just grabbing a beer before meeting Sammy,” Dean replied taking a seat on one of the red stools in front of his boss.

Bobby scoffed, “Alright, I just want to make sure you’re actually getting some kind of rest today.” He finished cleaning the glass he was holding, turned around to the tap and began filling it with Corona del Sol, Dean’s favorite.

Bobby flung a coaster towards Dean and set the glass down on top. He turned around to grab a bottle of Jim Beam and a whiskey glass, so he could pour himself a double before putting the bottle back on the shelf.

“You know, it’s frowned upon to drink on the job, Bobby,” Dean smirked as he brought the pint glass to his lips and taking a few swallows of the caramel colored liquid.

Bobby gave him a look that could melt metal. “Shut up ya damn idjit. This is my bar.”

Dean began to chuckle before throwing his head back and letting out a roaring, from the stomach laugh. After a few seconds, he finally caught his breath and took another sip of his beer.

“Whew, Bobby,” said Dean, dragging a finger across  the corner of his eye to wipe away a tear that had formed from the belly-aching laughter. “You sure know how to get me going.”

Shaking his hung head, Bobby picked up his whiskey and knocked the whole thing back in one go. He set  the glass down and poured himself another double, he looked at Dean inquisitively. He knew the boy hadn’t been right since his best friend left for Scotland, but there was an air that hung about him that gave the impression he was worse off than he was letting on.

“So, er – “ Bobby said as he fumbled with his glass.

“What?” Dean looked at Bobby with his big, mint green eyes as he pulled out his pack of Marlboros from his pocket and lit a cigarette before tossing the pack on the counter.

“Well first off,” replied Bobby as he was sliding an ashtray towards Dean and waving his hand through the air, dissipating the smoke. “Those things will fucking kill you.”

Dean chuckled, “You mean kill me  _ faster. _ ”

“You know what I mean,” Bobby said, rolling his eyes. “But I want to ask you how you’re holdin’ up.”

“I’m fine,” Dean shrugged.

“Well, you don’t seem fine, boy.”

Dean took a deep, long drag from his cigarette and slowly exhaled it out while ashing into the tray.

“Look Bobby, I’m fine. Honest.”

It was obvious the older gentleman was not buying a single word that came out of Dean’s mouth, but Bobby was in no mood to argue with him. Not that it would have done any good anyways. Trying to pull emotions out of Dean was like pulling teeth sometimes. Unless he was a few shots deep, all you were going to get was a great stone wall of ‘I’m fine’. So, Bobby let it go.

“If you say so.”

“I do,” Dean said taking another swig of his beer followed by a drag from his cigarette before putting it out in the ashtray. He pulled his phone from his back pocket and realized he still had quite a bit of time before having to meet up with Sammy, but wanting to avoid any more awkward chick flick moments _ , _ Dean decided to go ahead and jump on the train to head down to Brooklyn for the day.

Finishing off his beer and pulling out his wallet from his back pocket, Bobby suddenly put his hand on Dean’s arm stopping him.

“What the hell do you think you’re doing?”

The sudden physical contact caused Dean to jump a little before meeting Bobby’s gaze with a confused one.

“Wh-what?”

Bobby just started shaking his head. “Put your damn money away, boy. You’ve earned it.”

“Thanks,” Dean replied meekly. If it wasn’t for the fact that Bobby was his boss, he would’ve swore the guy treated him as if he were his own son sometimes.

Dean stood up from the bar stool to put his wallet and cell phone back in their pockets before grabbing his pack of cigarettes. Surrendering them to their rightful home in his jacket pocket. He waved goodbye to Bobby and strutted for the big, red door to begin his adventure to Brooklyn.

“Shhhhh-shit,” Dean hissed upon feeling the biting of the wind at his neck once again. He had almost forgotten how cold it had been outside. He turned around to see the door closing on its own and wished he could retreat back into the warmth of temporary shelter. God, he hated the cold.

He walked back up the stairs to street level, shoving his hands into his jacket pockets and wrapping his jacket in front of him. One would think he would’ve dressed a little warmer to face the New York weather at the beginning of November. He briefly pondered heading back upstairs to at least grab a scarf but laziness overcame him and he decided against it.

Dean started to walk down the block, heading towards the subway station. He kept his head down and watched each foot as it hit the pavement repetitively. Lost in his thoughts, he trusted his instincts to safely carry him to his intended destination. After several minutes, he glanced up to take a mental note of the distance left to cover only to realize he was already there.

Rounding the corner while heading down the stairs to the platform, Dean pulled out his wallet and fished out his MetroCard. Walking up to the turnstile he slid his card through the scanner, the remaining amount read $11.75 as he pushed on through and onto the platform. A subway train screamed by without stopping causing a force of cool wind to whip around the station.

Dean walked down a second set of steps, towards the tracks as he replaced the MetroCard back into his wallet before returning it to his pocket. He couldn’t lose that card if he wanted to get back home from Sammy’s that evening. Since Dean never really used the trains or buses except to visit Sam, he only added $20 at a time and replenished it when it ran out. As he leaned against a pillar, with his hands once again in the front pockets, he thought about how much time there was to kill before he met up with Sammy at his apartment.

_ Coffee wouldn’t be such a bad idea. _

There was a local coffee house right around the corner from Sam’s that had some of the best coffee Dean had ever tasted in his life.

_ Way better than that Starbucks shit. _

As his train grinded to a halt at the platform, Dean pushed himself upright and slowly walked up to the open automatic  doors that allowed passengers on and off the car. He stepped inside, gave a quick once over of his surroundings, and moved to the right to grab onto an overhead handle. The car wasn’t crowded by any means, but Dean still preferred to stand, which allowed people that wanted to or need to sit the capability to do so.

The subway conductor said something over the intercom that sounded like a bunch of mumbling and grumbling, then the car began to move. Dean watched as the platform slowly drifted from sight, before the train began to pick up some speed. It was about a twenty-minute ride give or take, depending on how many stops they made and any delays they might run into. After countless stops, the conductor came over the speaker announcing that they were pulling into Jay Street, which was just a few blocks away from Sam’s apartment. It always amazed Dean how short the train rides seemed.

The train slowed down to a stop and opened the doors to allow the flood of people coming and going from the train. Dean walked out of the train and onto the platform before heading up the flight of stairs to the streets. When the sunlight hit his face, he immediately brought his left hand to hid his eyes from the menacing rays that intruded his vision. As his eyes began to adjust, he reached street level and hooked right to fall amongst the shadows.

Dean walked past a few store fronts before stopping in front of Jupiter House. He paused in front of the big window of the coffee house and pulled out his pack of cigarettes. Setting the end of it between his lips, he pulled out his matchbook, stuck a match and glanced up. His vision caught a glimpse of a man in a tan trench coat walking away from him across the street.

His entire body tensed as he stared at the stranger trekking through the crosswalk . He had dark, untamed hair and was carrying a stack of books that seemed to keep him off balance. Dean was completely engrossed in this stranger when –

“FUCK!”

The match Dean had lite, before becoming entirely distracted, had burned down to his fingers, slamming him back into reality as it left a light singe across his thumb and forefinger. He quickly let go of the match, shook his hand, and stuck both fingers in his mouth while removing the cigarette with the other. When the shock of burning himself wore off, his eyes shot back up, scanning for the stranger that had caught him off guard, but he was nowhere to be found.

Dean slightly shook his head, shrugging off whatever the hell just happened to him, and tucked his unsmoked cigarette behind his ear. He pulled open the door to the coffee house, quickly walking inside. His thoughts still wrapped up in noticing a  _ complete stranger  _ that had completely captivated his attention, which was weird to say the least. That never happened to Dean Winchester. Never.

“Hi, what can I get you?”

“Uh, just a small coffee. Black.”

Dean handed over a few dollars, gave the kid his name, and stood off to the side to wait. He pulled his phone from his pocket to check the time. Ten minutes until 2pm, which meant Sam would be getting off the train in about thirty minutes. The barista called his name and set the coffee down on the counter. After retrieving the cup, Dean settled down at a table that allowed him to see out the front window in addition to taking a sip of his steaming coffee.

He sent a quick text to Sam letting him know where he was before bringing his full attention to the cross walk where he had seen that beautiful, stumbling stranger just moments ago. Dean sighed as he thought about the likelihood  of running into him again. Which was about one in eight million give or take. Especially in a city like New York. If you don’t jump at the opportunity, it is more than likely lost to you forever.

Dean never felt more alone in this gigantic city, then he did right then sitting by himself in a local coffee house, waiting for his younger brother to come home from school.

**Notes for the Chapter:**

> Hope you guys are enjoying this fic so far! There is much more to come, we just hit the tip of the iceberg!
> 
> All comments and criticisms are welcome! 
> 
> Thank you for reading :)


	4. Monday Morning

**Notes for the Chapter:**

> Whew! This summer has been busy for both my beta and myself. I recently acquired a new job that has taken some adjustment, throw in a couple trips to the ER, and her busy with her grad program, it's been a whirlwind. 
> 
> Here we are though! Chapter 4! I hope you guys enjoy this chapter as much as I liked writing it!

Castiel began to stir in his empty queen-sized bed as the new day began. The sun streaking in between the shades of his window, allowing the beams of light to dance around his bedroom. The dark blue cotton sheets and oversized black comforter had swallowed him up during the night, creating a cocoon effect around him. He rolled over, stretching his arms and legs, hearing some of his joints pop and feeling his muscles pull, before peeking out from underneath the covers at the faint red light screaming from his clock.

7:13am

Letting out a groan, he immediately rolled back over, put his other pillow over his head to shield him from the irritating rays that had started to pour into his sanctuary. He had woken up 2 minutes before his alarm went off. Those few minutes of sleep were absolutely necessary to get through every Monday.

Castiel had spent all weekend, hunch over, eyes strained, grading those papers for Professor Mills, and he was about to start the week all over again which meant more of the same. The Professor taught five different philosophy classes of all different levels, but thankfully, he was only required to be there for two of the classes, but had to grade the papers for three. It was part of his training to be a professor after he was finished with grad school.

He did get a minor break from reality while attending the after party of Anna’s march Saturday night. Even though he was forced into attending, Castiel did enjoy himself. They spent the evening on the rooftop of their brownstone apartment, drinking beer and wine, celebrating what Anna considered a victory at the march earlier that day. No matter how fun the night out is though, you truly pay for it the next morning.

Castiel woke up Sunday morning with a hangover from hell, as did everyone else. Meg ended up sleeping most of the day wrapped up in his bed, barely able to keep anything down. Anna and Gabriel had claimed the living room, sitting on opposite ends of the couch with their feet towards each other sharing a blanket, binge watching Netflix, and eating junk food. He spent most of his day taking care of Meg and using what little strength he had left to try and finish up the last few papers he needed to grade.

The alarm clock barely let out a chirp before Castiel’s hand came slamming down on it to shut it off. He didn’t even want to hear the usual beeping noises that alerted him to the start of his week this time.

7:15am

Sitting up in his bed, he swung his legs off the edge and pushed himself up. Lifting his hands above his head and leaning backward to give his midsection a good stretch, his t-shirt raised ever so slightly to expose his hip bones. Shaking out the rest of the tension from his arms, he walked over to his bedroom door and opened it to the living room. Anna was still asleep since her classes didn’t start until 10 that day. She tended to wait until the absolute last minute to crawl out of bed and rush down stairs towards the subway.

Strolling over to the kitchen, Cas began to fill up the coffee maker with water. Shifting three scoops of coffee grounds from the tin can and closing the lid, he switched the device to ON then spun around on his heels towards the bathroom.

Even though the bathroom the pair shared was rather small, it got the job done nonetheless. Being one that didn’t really enjoy wasting too much time getting clean, Castiel was in and out of the shower in just a few minutes. Standing on the bath mat outside of the shower, he glanced over to the mirror to give himself a once over. He had a smaller frame which let certain parts of his body appear more pronounced than others and he smirked as he gave himself a reassuring nod.

Preferring to air dry rather than use a towel, he crept over to the bathroom door and cracked it just slightly, sticking his head out to make sure the coast was clear. Over the years, Anna and Cas had some close calls when it came to wandering throughout the house in their birthday suits. They always managed to barely escape each other when it came to accidentally walking in on stuff like that, but even if they had, he doubted it would cause a riff in their friendship.

After a few seconds of glancing around the apartment, Castiel dashed across the hallway into his room and swiftly closed the door behind him. He walked towards his closet and pulled out a plain white button down, navy-blue tie and black slacks setting all three carefully on the bed. Bending down towards the set of drawers that were built into the back of his closet, he pulled out a white undershirt, navy dress socks and a pair of tighty whities.

He stood over his bed, bare assed, with his hands on his hips looking over his clothing choices for the day. Not that it made any difference, he wore basically the same color scheme, it was still something he enjoyed doing. He confidently slid his underwear on, followed by his slacks and undershirt then strolled out into the living room.

Greeted with the aroma of freshly brewed coffee, he entered the kitchen and picked a mug out from the cabinet above the coffee maker. Filling it up to the brim, he swung around pulling the milk out of the fridge.

_ God gracious _ .

He had forgotten to ask Anna to pick up another carton of milk on Saturday. Since this one was expired, he couldn’t dress up his coffee the way he liked.  He absolutely refused to drink it black.

_ Only psychopaths drink coffee black,  _ he thought as he pour the remainder down the drain. Castiel wasn’t entirely sure if that bit of information was true or not, but he had read it somewhere when he was studying psychopaths during his undergrad studies.  

Mentally cursing himself, he dumped out the cup he had just poured and decided to stop at Jupiter House to get his coffee. He deserved it anyway after the weekend he just went through. He decided to leave the coffee pot on just in case Anna wanted some when she woke up in an hour or two. Speaking of which, Castiel glanced at the clock.

7:54am

Damn, he had to be on the train into Lower Manhattan in thirty minutes to make it in time for his 9 o’clock class, and even then, that would be pushing it.

Quickly throwing on the rest of his clothes, Castiel began to gather the papers he had graded over the weekend and filed them into his laptop bag. Standing at the kitchen table, he mentally went through his checklist to make sure he had everything he needed for the day. Once one was on that train, there was no time to turn around if something was forgotten.

Calculating that he had everything ready to go, he quickly laced up his dress shoes, grabbed his apartment keys and cell phone. Cas then headed for the front door, grabbing his tan trench coat on the way out. He didn’t bother with locking the door behind, however, seeing as how Anna would be up soon and they lived in an apartment complex that predominantly housed students, there wasn’t a real reason too.

Swiftly scaling down three flights of stairs, Castiel soon was outside on the street. The wind immediately knocked the air back into his lungs causing him to lose his balance a bit before regaining his footing and setting off towards the coffee house. Tucking his hands inside the pockets of his trench coat to keep warm, he started to walk across the street, mentally sorting out the day that laid ahead of him.

After walking for two blocks, he rounded the corner and perked up when he saw the sign across the street that read ‘Jupiter House’. Castiel waited until the pedestrian sign signaled for him to cross, and even then, he had to avoid cars that simply ignored the traffic lights. New Yorkers were definitely not the best drivers in the world.

Successfully making it across the intersection, Castiel paused just briefly to check his watch before entering the coffee house.

8:17am

By some miracle, he was able to walk directly up to the counter. There were only about five people sprinkled about at the tables. A few of them had their laptops out, working on what appeared to be homework. The other few were simply sipping their coffee and staring off into the distance out the front window.

“Hi, welcome to Jupiter House. What can I get you?” The girl behind the counter smiled sweetly at him preparing to take his order.

Castiel looked up at the menu as if to study it, even though he got exactly the same thing every time he bought coffee here he enjoyed the idea of being able to change his mind if the occasion called for it. However, after a few seconds of empty staring, he shifted his gaze back towards the girl in front of him.

“Can I get a large vanilla latte with an extreme pump of espresso,” he replied as he started to pull out his wallet.

“Okay, can I have your name please?”

“Yes, uh, Castiel.”

She tilted her head slightly and giggled under her breath. “That’s an interesting name.”

Castiel looked up. His bright blue eyes meeting hers as the corner of his mouth twitched slightly. He was pretty sure she was attempting to flirt with him. He would have been flattered and might have even returned the flirtatious banter, but not having had any caffeine this morning, that was simply not going to be the case.

“Yeah,” he said as he handed her a $5 bill. “You can keep the change.”

He quickly stood off to the side to wait for his coffee, hoping that would be the end of the conversation with the girl behind the counter and checked the time again.

8:21am

If he wasn’t careful, he was going to miss his train and be late to his first class. Not that Professor Mills punished him or anything if he was late to class, but it reflected poorly on him, and that was something devastating in itself. If he remembered correctly, the next train into Manhattan left in seven minutes. He was going to cut it close, but he was sure he could make it in time.

Beginning to feel the pressure creeping up his spine, he looked behind the counter to see what stage the barista was at in making his morning drink, only to be greeted almost instantly with his latte.

“Castiel?” a man asked, setting the cup down on the counter.

Cas let out a sigh of relief, “Yes, thank you.”

Picking up the cup and making a b line towards the front door of the coffee house, he pushed past a tall man as he was exiting the establishment as well. The guy must have been over six foot easily with had chestnut brown hair that hung right around his shoulders. Carrying a black backpack over one shoulder, he had on a red flannel shirt and a black beanie. His dimples playfully etched into his face as he smiled at Castiel as he held the door open for him.

When he spoke, his deep voice almost made Castiel jump. “You look like you’re in a hurry.”

He looked up at the tall stranger and replied, “yeah, slightly. I’m trying to make it to the next train into Lower Manhattan.”

He walked out of the door, as the giant followed behind him as they both began to unconsciously move side by side in the same direction towards the subway station.

“I am too. Do you go to NYU?”

Castiel was rather put off by how nice this total stranger was being. Most people in New York, especially this early in the morning, did not talk to strangers. And why was he walking next to him?

His eyebrows rose as he pondered what this giant could possibly want, taking a swig from his coffee cup. Damn, that was some good coffee. “Yes, I’m in the grad program.”

The stranger’s eyes lit up like he had just won the lottery. They were kind, and innocent eyes. “Me too! Except I’m still a freshman. My name is Sam, by the way,” sticking out his hand for Castiel to shake as they continued walking down the street.

Looking from his hand, to his eyes, Castiel made a split-second decision that this ogre was probably harmless and took his hand, giving it a slight shake.

“Castiel.”

Sam gave a him a wide smile just as they began their descent down the steps towards the platform. “Nice to meet you, Castiel.”

As they hit the platform, one after another slid their MetroCards, and went through the turnstiles, Castiel thought that this day had begun to take an unfamiliar turn. Never had he just casually met someone and decided to ride the subway into town together. That was completely out of character for him. Sam seemed like a gentle giant and his internal alarms were silent, so he decided to lean into his instincts.

The train was already there waiting for them to board. Sam held out his hand to indicate Castiel to move onto the train before him, and he followed behind. The two stood side by side hanging on to the overhead railings as the train began to move forward.

Sam let out a low rumbling chuckle, “Looks like we made it right on time, huh?”

Castiel looked up at him and smiled, before taking a sip of his coffee. “Yeah, seems like it.”

They made the usual small talk as the train moved into Lower Manhattan. What’s your major? Do you like New York? How long have you lived here? What do you do for a living? Do you have a girlfriend?

“Yes, I do. Her name is Meg.”

“Yeah? You guys been together long?”

Castiel paused, and awkwardly shifted his weight from one foot to the other as he tried to nonchalantly take another sip of his coffee before replying. He was hoping Sam wouldn’t notice him mentally adding up the time.

“I guess, two years give or take.”

Sam’s eyebrows shot up. “That’s a good chunk of time, Castiel. Is it serious?”

“Yeah. I mean, believe so. I think,” replied Castiel, hoping that was the end of the conversation concerning his love life. Sam obviously picked up the hint that he didn’t really wish to elaborate on the subject and respected his wishes. While he still felt odd about telling a complete stranger bits about his personal life, it did feel good to shake up his normal everyday routine. He happily finished off the rest of his coffee as he thought about what the rest of the day had in store for him.

The train finally pulled into the station they needed to exit at, and opened the doors. As they made their way from the platform up to the street, they simply waved goodbye and went about their separate ways. Castiel checked his watch again, hoping that he still had time to make it up the stairs to his class without being too terribly late.

8:53am

_ Thank god,  _ Castiel thought as he rounded the corner from the station and entered the Arts and Sciences building of the university. He was lucky the subway station was right next to his building or he surely would’ve been late. He passed by the elevators and headed straight for the stairs. His classroom was on the third floor, but with so many students packing themselves into the elevators like sardines, Castiel felt much safer and comfortable climbing the stairs. The tight spaces and weight limit on the lifts had always made him uneasy when upwards of twenty students at a time would cram themselves in.

Just as he was reaching the top of the stairs he checked his watch one last time as he was rounding the corner, mere seconds away from reaching his classroom door. Almost running into a few students in the process of trying to mentally do to many things at once.

8:57am

Castiel opened the door to find the classroom already filled with the students who all lifted their heads to stare at who had just entered. Professor Mills was standing behind her desk setting up the overhead projector. She mimicked the action of her students and looked up at him, smiling.

“You’re late.”

Castiel felt a smirk pull at the corners of his mouth as he lifted his laptop bag over his shoulder. He set it down next to her on the desk, opening it to begin pulling out his laptop.

“Almost,” he whispered low enough so only she could hear, he didn’t want to undermine her in front of the class, and pointed to his watch.

8:59am

Professor Mills enjoyed the sarcastic banter between her and her TA and shook her head slightly and smiled. Castiel had been her favorite student during his undergrad program. That was precisely why she had asked him to be her assistant, she truly enjoyed his company and fully trusted him to do what she needed to be done. 

“What am I going to do with you Cas? Did you finish the papers like I asked?”

Castiel pulled out the stack of papers he has previously packed that morning and handed them to her with a twinkle in his eye and confidence in his chest.

“Of course,” he replied. “Did you expect anything less?”

“I only expect the best from you, Cas. And you have yet to deliver anything but.”

He immediately felt all the stress that had been weighing on his shoulders melt away. He was fully aware that this moment wouldn’t last forever, and he was going to bask in its glow for as long as he could. Today was going to be special.

**Notes for the Chapter:**

> All comments and criticisms are welcome!

**Author's Note:**

> Please read and review! All comments and criticism are welcome!


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